This is basically how I live my life. Throughout high school and freshman year college (I'm 19) I was always so concerned about things that were utterly unimportant in hindsight, like not offending people, making friends, not being a shut-in (I've always been an introvert). I've found that simply not caring about stuff has made the biggest improvement in my life satisfaction.

For example, I tried to make friends in the first week of college by talking to random people. I joined some clubs and went to events. This completely failed, I didn't click with anyone; these kinds of things didn't fit with my personality. All of my current friends I've met serendipitously. And, because I stopped caring so much about it, I think I have much better social skills now.

Kind of fits with the Daoist philosophy of wu wei: http://en.wikipedia.org/wiki/Wu_wei

EDIT: hah, looks like someone else made the same connection :D